Sodium borohydride → Benzyl [(1S)-4-[(tert-butoxycarbonyl)amino]-1-(2-hydroxyethyl)butyl]carbamate

HRID 1441982Notes

Reaction equation

HRID 1441982 reaction equation
C(=O)(OC)[O:2][C:3](=O)[CH2:4][C@@H:5]([NH:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[CH2:6][CH2:7][CH2:8][NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].[BH4-].[Na+]>O>[C:13]([O:12][C:10]([NH:9][CH2:8][CH2:7][CH2:6][C@H:5]([NH:17][C:18](=[O:19])[O:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:4][CH2:3][OH:2])=[O:11])([CH3:16])([CH3:14])[CH3:15]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86601682HCID 86601682, compound

Product 1

HCID 53795716Benzyl [(1S)-4-[(tert-butoxycarbonyl)amino]-1-(2-hydroxyethyl)butyl]carbamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The filtrate of (3S)-3-{[(benzyloxy)carbonyl]amino}-6-[(tert -butoxycarbonyl) amino]hexanoyl methyl carbonate (Example Z1) is added dropwise to a suspension of 0.49 g (13.14 mmol) of sodium borohydride in 0.6 ml of water at 0° C. The mixture slowly warms to RT and is stirred overnight. The reaction solution is concentrated, and the residue is mixed with ethyl acetate and water. The organic phase is dried over magnesium sulfate, concentrated and dried under high vacuum. The crude product is reacted without further purification.

Workup

  1. customslowly warms to RT
  2. concentrationThe reaction solution is concentrated
  3. additionthe residue is mixed with ethyl acetate and water
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. concentrationconcentrated
  6. customdried under high vacuum
  7. customThe crude product is reacted without further purification

Sources & evidence

ORD record
ord-172f78a93a8a4a7c90bfeba6d01894eb
Source dataset
uspto-grants-2010_02
Patent number
US07655643B2

Reaction notes

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